Find the Missing Context: Perspectives and Observations from Enterprise Experience with Daniel Lemire (2/4)

Nerd Journey: Career Advice for the Technology Professional

When you’re missing a specific experience in your career, how do you get it? Daniel Lemire was missing experience in a large enterprise to pair with the things he learned from pursuing a graduate degree. Join us this week in episode 324 to hear the story of what happened when Daniel got that experience that provided the missing context to apply what he learned.

Throughout this discussion, you’ll notice Daniel’s continued openness to new opportunities lead him from a contractor position in a large enterprise all the way to technical lead. There’s also a parallel process of Daniel’s development of expertise and credibility alongside his observations of the enterprise organization as a whole that encourage us not to limit our focus only to the technical work we’re doing. Near the end of our discussion, Daniel shares his perspective on an organizational decision to begin outsourcing and the way it impacted his work. What would you do in that situation?

Original Recording Date: 03-20-2025

Daniel Lemire is an AI Consultant working for ServiceNow. If you missed part 1 of our discussion with Daniel, check out Episode 323.

Topics – Missing the Context of Experience, Unexpected Opportunities, Confidence and Feedback, Enterprise Experience Meets Educational Background, Gaining Organizational Perspective, The Cascade of Objectives, Technical Leadership and a Change in Strategy

3:03 – Missing the Context of Experience

• Daniel said after completing his master’s degree at UNT he did not have the context of experience to pair with his education.
  • As part of the master’s program, Daniel got an education in marketing, management, and technology.
  • In class, they might have a discussion about how CIOs make decisions or have a guest speaker to provide additional context from the business world.
  • “I knew what the right questions were, but I didn’t understand why those were the right questions. And it was a real challenge for me because I couldn’t place what I was learning…. I was learning the right things. They really were the right things, but I didn’t know what to do with it. The curriculum I took in getting the master’s degree was exactly what I needed to be successful in a large enterprise. But because I had only ever done the independent consulting, I had only ever worked with very small companies, companies that had less than 100 employees…. So much of what I was learning about management discipline and program development and project management was for these really big organizations, and I didn’t have the context to understand why all of those things were necessary….” – Daniel Lemire, thinking back on his master’s degree program
  • Daniel makes a reference to the 150-person relationship limit known as Dunbar’s Number and says this requires very different business management techniques.
• Upon finishing the graduate degree, Daniel had learned 3 very critical things:
  • Daniel discovered through conversations with classmates and through completing specific projects that he had an aptitude for the subject matter. He also realized the program had been the right place for him.
  • Daniel knew he had a lot to learn but that he was missing enterprise experience. It was something he really needed to get the full value from what he had learned pursuing the graduate degree.
  • “The third piece of it that I didn’t understand until much later was that journey of taking turns between being overprepared for something and getting into something that you’re overwhelmed by. That’s yet another dichotomy because in some ways by getting the graduate degree I was overprepared for an enterprise environment, but from an interpersonal and from a political and…just being one of many in a corporation, I was totally unprepared for that experience because everything I had ever done up to that point was at a much smaller place.” – Daniel Lemire
    • Daniel was the only IT person when he worked at the Conroe Medical Education Foundation, and there were only about 20 employees.
    • Through his consulting work building websites, Daniel interacted with several companies across various industries. He mentions one of the largest had about 80 employees.

6:54 – Unexpected Opportunities

• Daniel shares a story of crossing paths with an acquaintance who had been the systems administrator at the Texas Women’s University (TWU) Police Department but was moving to a different job.
  • “Sometimes you find somebody else that’s technically good and you know who they are, and you remember them. This was kind of one of those deals…. I’m doing this grad school thing while I’m kind of just paying the bills doing the consulting thing. So, I was ready to take on another opportunity.” – Daniel Lemire, on a chance meeting with an acquaintance who got him a job
  • Daniel was asked if he’d be open to doing something different and possibly taking over at the university police department. After saying yes, Daniel spent a year working at TWU while he finished his graduate studies, which provided the opportunity to learn about a completely different type of business (a police business).
  • Daniel spent time understanding what the police officers did and spent time building systems. One specific example of a system Daniel built (or contributed heavily to building with others) allowed students to buy a campus parking pass on the university’s website. This was his first experience working on an integrated system.
  • In everything he did, Daniel’s intent was to solve problems. There wasn’t a guidebook or manual to build things like integrated systems. Another example of a project from his time at TWU was building a customized alert system for the university based on programmatic scripts (which acted as a stop gap until a vendor solution for this could later be put in place).
  • “There’s no guide for this. I just know what the technology can do, and I know what my skillset is. We put the things together and built something that solved an immediate issue…. Even TWU as big as it was…I was just in the police department. That was a big place, but my place inside that big place didn’t take advantage of everything I’d learned in getting the grad degree.” – Daniel Lemire
• While Daniel was working at TWU and wrapping up his graduate degree, he received a call from a gaming buddy from his time as an undergraduate who suggested he consider a role at PepsiCo.
  • The role Daniel’s friend mentioned was a contract role for loading operating systems on servers before they get shipped to specific sites. His friend’s description of the role was a little nebulous.
  • As a result of their discussion, Daniel got connected with the recruiter for this role. He was intially worried about asking for too much money but found what he asked for was in range per the recruiter. Daniel was really excited about the possibility of a full-time role.
  • After Daniel was passed along to the hiring manager to interview for this role, the manager asked him how he felt about working weekends during the interview. Daniel was honest and communicated working on Sundays was not something he could do. After the discussion with the hiring manager, the recruiter called Daniel to let him know it wasn’t going to work out and that this was a weekend job (not something that was previously communicated to Daniel as part of the process).
    • “This isn’t going to work out because this actually is a weekend job. And I didn’t know that. That wasn’t disclosed in the conversations she and I had or in the job description details that were in front of me. I was just answering the questions honestly because that’s what the right thing to do was. That job didn’t work out for me….” – Daniel Lemire
    • Daniel could not commit to the schedule for this role because it conflicted with his church activities.
• A few months later, the same recruiter called Daniel saying there was another open position for which he might be a fit. This role was better pay than the first one he had interviewed for and was more focused on the systems engineering work Daniel had been doing.
  • This job ended up being a role on the same team as the friend who recommended Daniel apply at PepsiCo. Daniel’s friend removed himself from being part of the interview process to prevent conflicts of interest.
  • Daniel built a good rapport with one of the decision makers and was hired quickly as a systems engineer. He started with PepsiCo working on Windows Server automation. Daniel was considered analyst level and not a lead engineer.
  • Daniel says he had been doing more programming and coding than working with hardware coming into this role, and he was able to learn a great deal in this role.
  • “That then was a huge opportunity for me because I got to get into something that was completely new. The hardware focus was something that I wasn’t used to…. I got to go deep into something I thought was going to advance my career because I didn’t know enough about hardware. I got to work on a team inside of an enterprise, and I really wanted that enterprise experience after I got the grad degree because I had all of this stuff in my head that I couldn’t really quite use yet.” – Daniel Lemire
    • At TWU, there was no need to decide which server vendor to use. A specific vendor was the established server provider.
  • The paycheck for this job was a great opportunity for Daniel to provide steady income for his family. They were able to buy a house and discuss starting a family.
  • There were opportunities all over the place after starting at PepsiCo. Getting in and doing well could set someone up for a career there rather than just a job.

15:14 – Confidence and Feedback

• When Daniel was only doing consulting work, he was not around other people doing the same type of work outside of some mentors who provided guidance. Being in the graduate program put Daniel around other people doing similar work and helped him understand he had the ability to do well in this field. It produced a confidence that seems to have catapulted him through the interviews for roles at PepsiCo.
  • In the last couple of years Daniel has learned how essential confidence is in getting us to what’s next.
  • Daniel has seen a number of people be overconfident and run into numerous problems as a result. A sensitivity to these kinds of people may have affected the way he thought about confidence in the past.
  • “Finding the way to get yourself the self-confidence so that you can convey what you know to other people enables you to explain the value that you can create for them, and that’s how we do business together.” – Daniel Lemire
• Nick mentions an element of feedback as well throughout Daniel’s story from teachers and friends. His friend recommending the role at PepsiCo is the next iteration of that feedback.
  • Daniel tells us he was not seeking feedback early in his career, but he was getting it.
  • “If you asked me about it now, I would expressly tell you that feedback is probably the most important element of being successful. It’s going to give you an early warning sign when you’re on the wrong path, and it’s going to push you in the right direction when you’re on the right path.” – Daniel Lemire
  • Daniel remembers a book he was reading back when he and his wife were dating that encouraged only dating people you are serious about. Otherwise, it is a waste of time. Daniel says feedback is how you prevent wasting your time.
  • In Daniel’s case, feedback he received was unsolicited early on. Nick has heard podcasters say that getting no feedback (good or bad) about your podcast is a bad sign.
  • Daniel works from home and puts post-it notes on his monitor that only he can see. One of the notes says, “what experiments are you doing?”
    • “In the absence of feedback, you can do experiments and see and evaluate yourself. Is this moving me in the right direction? …The reality is it creates the delta between what you’re doing and what you could be doing…. If you are changing things, generally you are going to get a response. Either somebody’s really going to like it, or they’re really going to hate it. But either way, you’re going to get some feedback.” – Daniel Lemire
  • John says a corollary to not getting feedback is perhaps no one cares enough.
    • Even if someone cares negatively and thinks you’re wrong, at least someone cares enough to criticize and maybe set you on the right path.
    • “Whatever you’re doing, make a ripple.” – Daniel Lemire

20:39 – Enterprise Experience Meets Educational Background

• Once Daniel started working in an enterprise environment at PepsiCo, did everything he had learned in his graduate program start to click with his experience immediately, or did it take a while for that to happen?
  • “I can tell you that basically from the moment I landed, everything started to make sense about that grad degree…immediately. I felt like I was Superman and had X-Ray vision because everywhere I looked the pieces were fitting together…. The part that I didn’t appreciate about knowing all of that was the engineer in me was also immediately frustrated because I could see where things were broken, and I wanted desperately to fix them.” – Daniel Lemire
  • Daniel was able to understand how upper-level leaders were making deicisions thanks to what he had studied. As someone new to the organization, it was important to execute his job well and build credibility. Credibility was necessary for speaking up later in attempts to impact organizational decision making.
  • “I’m delighted to say that was the easy part. Being good at the thing that I was responsible for was what allowed me to consistently exceed the objectives that were handed to me. And to a large degree they were handed to me…especially in the early days of making any kind of decision about how things were going to work. It was just ‘this is what we need to accomplish. Go get it done.’” – Daniel Lemire
    • Daniel enjoyed writing code and working in the server lab to make things work.
    • He was a contractor in the beginning and was left out of organizational politics. Daniel reminds us that contractors should stay out of organizational politics because it can lead to trouble.
    • Daniel did well in his role as a contractor and was helpful to the people around him, earning a reputation that would get him to full-time employee status about 1.5 years later. Daniel even did well enough to negotiate a little bit on his full-time employment offer.
    • “I could that time as a contractor as my time at PepsiCo because, really, the things that I was working on were my responsibility. I owned the thing that I was given.” – Daniel Lemire
• Though it no longer removed him from politics of the organization, being a full-time employee meant Daniel got to be part of the progression and accomplishments of a large enterprise. He enjoyed seeing the datacenter and how computing was handled at the scale of the organization’s needs.
• Daniel knew the combination of growing himself, doing the technical things that needed to be done, and leveraging his graduate degree would help him progress within the organization. The company made investments in Daniel as an employee in the form of training, for example.
• Was this Daniel’s way of answering the question from the person at church from long ago about what he was doing to grow himself?
  • Yes – it’s about having a vision and intention for where you want to go in the future to avoid standing still.
  • Daniel brings up the physics concept of entropy. Standing still means you are degrading.
  • “You’re always in some phase of change, so if you have any control at all, make sure that your phase is going up and not down. Because if you’re not paying attention to it, entropy is playing on the system, and things are going to naturally degrade.” – Daniel Lemire

25:10 – Gaining Organizational Perspective

• John mentions Daniel’s first experience in an enterprise was in a very large one. For very large enterprises, it takes a lot of time and effort to move in a direction the organization is not already moving (i.e. the container ship analogy). How did Daniel see this in his experience?
  • Daniel started in an individual contributor role. He was not responsible for a program or for people. The graduate degree gave him the context to interpret different situations within the company.
  • “In any sufficiently large environment there are the official things, the things that everybody says because it’s what they have to say or it’s the dialogue they have to carry through. Then there are the things behind the scenes, the real actual games that you’re playing, and there’s a whole different set of rules that are associated to that. And the sooner you can understand the difference between the rules they say they’re using and the rules they’re actually using, the more likely you are to be successful. And to me, that graduate degree gave me to tools I needed to understand not just what was said but what was not said and what that meant for me. So even though I didn’t have that responsibility, I could see the things that were being done from an organizational perspective and translate that into being able to decipher what the bigger next move was.” – Daniel Lemire
  • In Daniel’s role as an individual contributor, he knew they needed to iterate on a server build or support new equipment with hardware refreshes over time, for example. The technology strategy of the organization and business leader perception of the technology organization were things Daniel could still observe in his role.
    • “I was able to see both the good and the bad from a position that I could learn a lot without having to carry any of the responsibility about making those decisions. And I think that was really the thing that shot me ahead from my enterprise career perspective…. I was able to gather a lot of information in a very short period of time because I was able to contextualize it with the graduate degree.” – Daniel Lemire
    • Many of Daniel’s peers who didn’t have the same education had trouble making sense of things the company was doing (i.e. why decisions were being made certain ways), even to the point of frustration at times. Even if Daniel didn’t agree with a decision, he could contextualize it and understand it.
  • Did Daniel try to explain some of what he knew / understood about the organization from his education to his colleagues, or did that feel too assumptive?
    • Daniel says he’d be willing to have a 1-1 conversation with people about his observations.
    • In the audience of an entire team or a senior leader, Daniel held his tongue. Looking back on it now, Daniel thinks he could have provided more value by sharing some of his analysis of the situations with others.
    • “…I did have some of the right ideas, but what I didn’t have that I now fully comprehend is I didn’t know how to say things in a way that would be received well. In other words…my early days…while I was good at providing critical feedback, it was critical feedback. I didn’t know how to say things in a way that was polite or nondestructive…. I had some critical moments in my career where I had some very critical feedback, and I let it out in a way that was not constructive or useful. And that limited what I could do from a career perspective…. So, it’s kind of one of those double-edged swords. Don’t bite your tongue unnecessarily, but at the same time, be sure that you can say it in a way that is constructive and helpful.” – Daniel Lemire
    • Daniel says the internalization of frustration has come out in his tone at times. Even now, Daniel has to be mindful of not putting himself in a situation that is overly stressful or frustrating because those conversations don’t usually go well.
    • Daniel might have known the right thing to do but didn’t know how to convince others or use what he knew to persuade them.
  • Daniel highlights how valuable it was to bounce ideas off his peers within the company.
    • We can easily recognize who knows their stuff / area really well and might seek these people out for a discussion.
    • It’s important to be really good at what we do. Daniel says it can lead us to new opportunities because people seek us out as experts.
    • “That’s why you have to balance the doing the things that you’re not good at and exercising the things that you are good at. If you get too far into the doing things that you’re not good at, it lessens the number of opportunities that you have. So, you have to be really strategic about diving into the deep end too far. You have to continue to do the things that you’re not good at but do it in a way that leverages the things that you are so you don’t get into the red zone. That’s one of the things that I’ve learned, and we’ll touch on that a little bit later…. The very first thing I took away from that experience was find the right people and talk to them on a 1-1 basis…. Finding great people is a huge career builder.” – Daniel Lemire
    • Talking to the right people 1-1 allows you to test out what you’re seeing and get some feedback. Also, these discussions allow you to identify who you can work well with to take advantage of it later on in your career.

33:42 – The Cascade of Objectives

• Does finding the right people mean building champions for your personal brand?
  • Daniel says yes – this idea of brand building is true everywhere.
  • “You have to be able to tell someone in a very short period of time what your value is, and that is your brand, no matter what you’re doing, no matter how large or small the organization is. You do have to think about that to some degree and have a plan for that. That’s something I lucked myself into.” – Daniel Lemire
  • Daniel can look back and see that he was doing the right things to build a strong personal brand early in his career, but he didn’t quite understand what he was doing at the time.
• Nick thinks most people do not know how to succinctly articulate the value they bring to situation / job / role without some reflection, writing, etc. We can get some of this from the feedback received from others.
  • Daniel was having conversations with other people 1-1 but was not consciously thinking of what things he was doing should be put on his resume.
  • Daniel worked for a company which required employees to write down and track their yearly objectives (including evidence of progress made to reach those objectives). This helped him think through resume-type items. It is a benefit of working for large organizations (mandates to use specific systems to complete these types of exercises).
  • “I can honestly say with reflection that that’s one of the best things an organization does for their employees because it forces you to do something that will make you better whether you want it to or not…. If you’re in a position today where you’re not given that system, the best thing you can do for yourself is to literally write it down. What are you going to do? And then look at it again multiple times to ask yourself ‘what am I doing about that’ and ‘how did you do so far?’ The most successful people write it down. They think about it. They talk about it, and then they write it down and then evaluate it later. And that is so essential, and I didn’t really appreciate that until just recently.” – Daniel Lemire
  • John mentions in his most recent role he was asked to go through the OKR (objectives and key results) process. He had done this before at Google.
    • In a leadership position it can be harder to take OKRs from an upstream leader and then re-contextualize for downstream team members. But it does provide a common understanding of how everyone will be measured.
    • John agrees writing and tracking objectives can be a great resume builder. It helps someone articulate how they were measured and the steps they took to accomplish the objective(s).
    • Daniel calls this process a cascade or translation of the objectives down to a manager’s direct reports. This process was one of the most difficult things for Daniel when he was a people manager (the translation process).
    • “Whether or not you’re great at it, you have to do it because if you are not doing it, the people that you’re responsible for supporting and helping don’t get the context that they need for why it is they’re doing what they are doing…. Just improving yourself in a vacuum is actually one of the biggest roadblocks to organizational success…. That’s what a critical manager does…they make sure that the individual is able to grow and carry through the responsibilities but to do it in a way that it doesn’t jeopardize the rest of the system. So, in some ways you might say that those middle managers are the transmission that connects the engine to the wheels. You can have a great engine, but if it never gets connected to the wheels, you’re not going anywhere.” – Daniel Lemire
    • When people get really good at building their own thing, it might not interface well with the rest of the organization.
    • Daniel mentions he sees many people get excited about what they can do with AI. It may be empowering to an individual, but we might want to jump in to make ourselves more effective without considering the larger organizational impacts doing this will have. A senior developer might be able to build great applications with AI (perhaps even using AI for the things they might ask a junior developer to do), but not working with a junior developer means the person is not being fostered to develop into a senior developer. There’s a downstream impact here that comes up later on.
    • “The other thing that as individual contributors and managers that we should all be thinking about is, ‘how do I optimize for today without putting myself in a difficult situation for tomorrow?’ We have to think about both the short and the long term, and we have to help the rest of the organization do that as well. That’s probably the challenge for the next decade as we get the most advanced technology that man has ever seen and try to put that together with humans.” – Daniel Lemire

41:05 – Technical Leadership and a Change in Strategy

• What made Daniel move toward people management in the first place? He shared some insight into this earlier, but we want the full story.
  • The first step in the process was moving from build engineer to technical lead. Daniel tells us he was not responsible for managing direct reports in this role but focused on making a greater impact on the overall team and the work they were doing.
  • Daniel says progressing to technical lead was a natural progression. When he looked around, Daniel once again realized he had an aptitude in this area. After observing the systems and the way work was done, it naturally led Daniel to persuade members of the team to take slightly different approaches that were more optimal. It was about influencing the direction of the work people on the team were doing and how they were thinking.
  • Daniel shares an anecdote from his COBOL class in college. When students were getting caught up in small details, the professor commented that the class “couldn’t see the forest for the trees.” The professor reiterated to the class that they were focusing too much on the small details and not thinking about what they were trying to accomplish.
    • The above is exactly what kept happening in Daniel’s technical conversations with others. Daniel had to encourage people to look at the larger picture, and it kept happening.
    • “And that just sort of kept happening. It was just sort of a natural progression to where I was helping them with those individual things that they needed to accomplish but also helping to make things mesh more easily as we had to put things together because I was consistently finding myself in the situation where I had to negotiate the interface between the work that we were doing and the value that it was creating. I didn’t understand that at the time, but that’s actually what I was doing now reflecting back on it.” – Daniel Lemire
    • Daniel might have to tell someone that reprogramming a specific function again and again was not going to deliver the results the team needed (build a server faster). Sometimes an optimization we are making will not improve the system, and value only gets generated when the system is improved.
  • Daniel says he spent the middle decade of his career in that contextualization area we spoke about earlier. He was at PepsiCo for nearly 16 years.
    • The first couple of years were getting technically oriented and finding ways to contribute to the team.
    • The career progression of others gave Daniel the opportunity to move up / progress within thr company. Daniel would ask for specific work / projects, and his manager could see his talent and would in the future look for opportunities to leverage those talents.
    • “They understood that I was capable and that if they gave it to me, it would get done well. That made things better for them, and that made things better for me.” – Daniel Lemire
    • In being the technical lead, Daniel appreciated that he did not need to deal with HR things. In this role he was able to accomplish a number of things he is very proud of but also limited his growth from a manager perspective.
    • “I don’t have any regrets about not moving into that manager space sooner…. I was able to observe all of that without having to be responsible for it. For me, that responsibility is a mantle that I want to put on, but when I do put it on, it is something that weighs me down. There is a cost for me in taking on that. I take it very seriously.” – Daniel Lemire
    • Daniel stayed in the technically focused contributor role for a long time. He did not have to take on being someone’s manager and existed to support others technically and to help them grow.
  • It was the organizational strategy inside the company that started to affect Daniel’s career trajectory.
    • There was a lot of outsourcing happening for various reasons (optimization, globalization, etc.), and it impacted Daniel’s colleagues over time and the relationships he had built with them. The changes meant Daniel had to seek out new people to work with on various projects, and instead of working in the same office as Daniel, these people were in a different part of the world and from a different culture.
    • “You’re building your network. Every person you have a good rapport with that goes somewhere else…that creates totally new avenues of opportunity for you.” – Daniel Lemire
    • Daniel was frustrated that colleagues had to leave the company, but he also had work to do and decided to focus on what needed to be done (the things he could control). This was building Daniel’s frustration in ways he did not understand at the time.
    • Daniel says he often tries to compartmentalize things and uses the analogy of a waffle to illustrate.
    • “Don’t think about just work or just family. Sit down and think about all of the elements of your life and how they are going to fit together. Because if they don’t fit together, it will come around to bite you later.” – Daniel Lemire, on compartmentalization
    • The organization’s decision finally impacted Daniel. The company decided to outsource all infrastructure services. This was a very challenging time for Daniel. He had to hand over systems and processes he had built to someone he had never met. It was a difficult reality but a reality he had to face.
    • “It was to the point where my management team actually said to me at one point – ‘Daniel, you don’t do that work anymore. That’s not yours. That’s not your job. Your job is to make sure that things get done, not how they get done.’ And I had a really hard time with that…. A big part of my pride was the work that I had produced. Essentially, what that meant to me was that the work that I had done, that I had spent the better part of a decade to be effective at, really was not valued…. There was a time of struggle there for me, and that began the sort of searching mode…going back to the very early experience where I found out…that’s not where I’m going to be now. Now what? And it was because I recognized that what I was doing was no longer the path forward, I kind of had to have a reset.” – Daniel Lemire

Mentioned in the Outro

• It sounded like gaining the enterprise was the right place for Daniel. Doing his work well was the groundwork for developing a great reputation, but Daniel was also observing the organization and looking at the way decisions were made. At first, he did not have the influence to change any decisions, but he got at least some influence at the technical lead level.
  • This began with remaining open to new opportunities just like in his early career (i.e. recommendations based on the feedback from others). As he started to observe the enterprise of PepsiCo, he began looking for new opportunities inside the company. These types of opportunities didn’t exist at the companies where Daniel had worked previously due to their size.
• Does your company have you set and track objectives? If so, are you doing it well?
  • If you don’t have this requirement, you can still document objectives and progress toward them on your own.
  • Maybe we should document and track our experiments too. Nick thinks we should still track things even if they initially seem unrelated. They might be more relatable to your next role than you think!
• Other episodes that pair nicely with this episode:
  • Episode 284 – Draft Your Narrative: Writing and Building a Technical Portfolio with Jason Belk (2/2)
    • Jason Belk reminds us of the importance of a career narrative. We need documentation of the work we are doing to generate and practice that narrative!
  • Episode 267 – A Theme of Learning with Erik Gross (1/3)
    • Erik talks about a moment when his classroom learning in the Nuclear Engineering program met experience.

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